As John said the business end of the TOB is the face next to the engine. If it's grease soaked, smooth, flat, and not cracked or chipped you're good.
As far as lubing the pilot bushing, the steeper the better. Anything pointed down hill is OK. The idea is to get the lubricant to run down the shaft lengthwise and into the pilot bushing before it runs around the shaft, diameter wise, and drips off. That's why steeper is better. This is also not the time to hold your finger on the button for two or three weeks
there is a clutch in there as well that really shouldn't get lubed.